We’re hiring a Chief of Staff to work directly with Nina, Float’s SVP, Go-to-Market, as her closest strategic partner. This is a builder’s seat: you’ll shape the GTM operating model, the cross-functional handoffs, and the way priorities get set and tracked rather than stepping into an established playbookYou’ll move fluidly between big-picture strategy work and hands‑on execution, sometimes in the same afternoon: shaping the quarterly GTM narrative for the leadership team one day, driving cross-functional initiatives the nextOwning the GTM operating rhythm: business reviews, OKR tracking, and leadership/board‑ready reportingBridge strategy and execution across Product and GTM, ensuring cross‑functional priorities translate into coordinated action and measurable outcomesOwn and maintain single sources of truth, ensuring key information is accurate, actionable, and surfaced to the right stakeholders at the right cadenceTurning ambiguous priorities into structured plans with clear owners and timelinesDriving cross‑functional initiatives that span Sales, Marketing, Partnerships, and Customer Success, the ones that don’t sit neatly under any one functional leaderHelping connect strategy and execution between Product & GTMActing as a trusted thought partner and occasional filter, helping the SVP focus time and energy on what matters mostRepresenting the SVP in rooms she can’t be in, with enough context to make sound calls in real timeHelping build the GTM org itself as it scales: interview processes, onboarding, team rituals and everything in betweenBenefits
Competitive coverage of medical,



dental and vision insurance for employeesEducation & learning stipend for personal growth and developmentFlexible vacation timeWork from home stipend to help you succeed in a remote environmentIn a nutshell, you’re an activator. You instinctively know where momentum is needed, bring the right people together, and facilitate the conversations that turn ambiguity into clarity and ideas into execution. You’re a trusted thought partner who helps leaders move faster and make better decisionsBased in Toronto and excited to work closely, in person, with the SVP and leadership teamExperience at a top‑tier technology company or fintech, with a strong understanding of how GTM strategy and execution differ in regulated, trust‑driven marketsThrive in high‑growth environments where priorities evolve quickly, and you’re energized by solving the company’s most important problems, regardless of whether they’re inside or outside your formal remitExceptional at bringing structure to ambiguity, with a proven track record of taking loosely defined problems and translating them into explicit plans with measurable outcomesAn outstanding communicator who can seamlessly shift between writing board‑ready narratives, executive briefs, and concise updates that drive alignmentAI-forward and relentlessly curious. You continuously improve the way you work, leverage AI to accelerate execution, and champion practical AI adoption to help the broader team become more effectiveHighly analytical and comfortable working with data, but focused on using insights to drive decisions and action, not just build dashboards5+ years of experience, ideally combining management consulting (strategy or operations) with hands‑on operating experience in a GTM function such as Sales, Marketing, Revenue Operations, or Business Operations
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📌 Chief Of Staff (Winnipeg)
🏢 Float
📍 Winnipeg